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24 Photos
HART REALTY
$419,900
4 BD | 3 BA
Residential - Single Family

Beautiful views and move-in condition! This home has a new kitchen with SS appliances, stone countertops, tile back splashes and slider to the 2 tiered deck overlooking Noble farm fields. Relax and take in nature's beauty! There are all new floors, interior and exterior paint, and extreme low temp high efficiency heat pump/Air conditioning. Updated 2.5 bathrooms and a 2 car garage make this home everything that you need.


51 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$426,900
4 BD | 2 BA
Residential - Single Family

New and Improved! Lovely finishing touches to make it sparkle and shine and move in ready! New roof, fresh exterior paint, new energy efficient mini splits for heating and cooling and Mass Save Insulated for low annual utility cost, new 200 amp electric service, updated baths, full-length front porch perfect for relaxing or socializing. Be welcomed onto the glorious front porch wonderfully inviting facing west for incredible sunsets and a sneak peak view of Bousquet Mountain. Inside, a gracious entry leads to a classic living room with built-in bookcases, window seats. Gleaming oak floors flow throughout. The formal dining room with a butler's pantry with a coffee bar and fridge nook. The kitchen features new hardwoods, a darling everyday dining nook with built-in for the cookbook


43 Photos
SIGNATURE ASSOCIATES
$429,400
4 BD | 2 BA
Residential - Single Family

Lovely, meticulously maintained home in southeast Pittsfield offers spacious living. Attractive kitchen with large dining area leading to deck. Generous yard with fenced area for pets or kids, a garden area, large shed. There is an ''in-law'' arrangement in the lower level that has living room, bedroom or dining room, a den or dining or bedroom, kitchenette, full bath and door to the garage.Three bedrooms on first floor with nice closets, and there is a full bath. 2 car garage with work area. Come and see this home! Open house 10/25 10:30-12:30


67 Photos
COHEN & WHITE ASSOCIATES
$430,000
3 BD | 2 BA
Residential - Single Family

Exceptional opportunity: Fully renovated three-bedroom main residence with guest cottage...FULL DELEADING COMPLIANCE!!! This special property offers owner-occupied living and additional income. The fully renovated main residence with the separate guest cottage provides ample space for various living arrangements. Both homes are move-in ready!


66 Photos
COHEN & WHITE ASSOCIATES
$430,000
3 BD | 2 BA
Multi-Family

Exceptional opportunity: Fully renovated three-bedroom main residence with guest cottage...FULL DELEADING COMPLIANCE!!! This special property offers owner-occupied living and additional income. The fully renovated main residence with the separate guest cottage provides ample space for various living arrangements. Both homes are move-in ready!


7 Photos
KEY REALTY

Discover the ideal setting for your next home or retreat on this 15-acre parcel in West Pittsfield. Thoughtfully prepared, the property already features installed electricity, along with a newly constructed driveway and building pad. Enjoy a perfect blend of open and wooded land, including 5+ acres of fields, 10 acres of forest, and approximately 700 feet of road frontage.With city water, multiple perc-tested building sites, and beautiful mountain views, this property offers exceptional flexibility for development. Perfectly situated between Pittsfield State Forest, Onota Lake, and Pontoosuc Lake, and only five minutes to downtown Pittsfield, this is a rare opportunity to own a substantial piece of land in one of Pittsfield's most scenic areas.


40 Photos
BARNBROOK REALTY, INC.
$439,000
6 BD | 3 BA
Residential - Single Family

**BRAND NEW ROOF BEING INSTALLED!**Beautifully renovated multi-zoned building has huge potential for residential use. Centrally located and just minutes to downtown Pittsfield and all Berkshire cultural venues. This fabulous building has been updated with modern amenities and chic decor! This home offers an enormous kitchen area with washer & dryer, 6 bedrooms, 3 full baths, 4 fireplaces and oversized spaces that flow from one room to the next. Superb for entertaining large groups! Natural light floods this home. Original hardwood flooring and quality craftsmanship throughout. New mechanicals & electric.Nothing to do but move in! Has outstanding Rental history as well! Ample private parking in rear of building.Being sold completely furnished.


39 Photos
BARNBROOK REALTY, INC.

Beautifully Renovated Prime Investment Property, centrally located and just minutes to all Berkshire cultural venues. With the most updated chic decor, this downtown multi-use property has rental success with local corporations. This stately victorian has been tastefully updated with modern amenities. Offering 6 bedrooms, 3 Full baths, 4 fireplaces, expansive common areas, oversized renovated kitchen with 2 refrigerators. Rooms are complete with high end furnishings and appointments. Lovely huge spaces flow from one room to the next, with plenty of natural light. Original hardwood flooring and quality craftsmanship throughout. Ample private parking in the rear of the property. New mechanicals and electric. Investors can hit the ground running in this '''Turn Key'' Investment property


46 Photos
413 REAL ESTATE
$439,900
4 BD | 2 BA
Residential - Single Family

Welcome to this spacious and inviting 4-bedroom home, perfectly situated in a desirable neighborhood. Move-in ready and full of charm, this home features wood floors in the main living areas and a cozy gas fireplace that adds warmth and character to the living room. The first-floor primary bedroom offers convenience and privacy, while three additional generously sized bedrooms are located upstairs. The finished lower level expands your living space, complete with a stylish bar area perfect for entertaining. Enjoy outdoor living in the fully fenced backyard, featuring a shed for extra storage, a large deck, and a gazebo--a perfect setup for relaxing or hosting gatherings.This home offers the perfect blend of comfort, style, and function. Don't miss your chance to make it yours!


19 Photos
ROYAL PROPERTY GROUP

Turnkey 166.7 kWAC solar field on 1.25 surveyed acres in Pittsfield, MA. Ground-mounted, fully owned system with 784 panels, 5 SolarEdge inverters, and direct grid tie-in via oversized 400A service. Averaging $141K/year in gross income from energy sales and SREC credits. Minimal operating costs, transferable SREC II program (through 2027), and included spare components. Ideal for investors seeking reliable clean energy cash flow with future potential for residential development. No leases--fully owned land with easements in place. Once in a lifetime fully operating solar purchase. Would be an excellent investment. With right terms seller is also willing to hold paper.


45 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$450,000
4 BD | 3 BA
Residential - Single Family

This well-cared-for colonial home has been cherished by the same owners for over seven decades and is ready to welcome its next chapter. The first floor offers a spacious layout with a large kitchen, dining room with access to a seasonal porch, a living room featuring a wood-burning fireplace, a family room with half bath, and a four-season sunroom surrounded by windows overlooking the backyard. Upstairs, the primary bedroom impresses with double closets and a vaulted ceiling, complemented by three additional bedrooms and a full bathroom. The fully finished basement provides valuable extra living space with a laundry room, 3/4 bath, and game room. Recent updates include a new roof (2021), heating system (2023), and refinished floors with fresh paint (2025).


2 Photos
BLOOMBERG REALTY, INC.

Yes, the Jim's House of Shoes building is for sale! Great location in the heart of North St, downtown Pittsfield. 4 large front display windows, 3 entrances and exits, full, usable 5,500 sq. ft. basement with inside access. Start a business here; move a business here; be part of Pittsfield's rejuvenation!


44 Photos
BERKSHIRE HATHAWAY HOMESERVICES REALTY PROFESSIONALS-WESTFIELD
$459,900
4 BD | 2 BA
Residential - Single Family

Motivated Seller.! A home that is in move in condition Prestigious grand colonial located in the lovely Southeast area. This home has been meticulously maintained. Four large bedrooms, formal living room with fireplace, Glass doors leading out to a pergola, A family room, dining room, renovated kitchen , den or office could be a fifth bedroom. One upstairs bathroom renovated and one on the first level,The landscaping is a gardener's dream come true.A Berkshire County haven. Walking distance to theaters and great downtown eateries and coffee shops. Close to Rt 7 which leads to Lenox, Tanglewood Stockbridge Red Lion Inn.. Great Barrington. Skiers vacation spots. Words cannot describe all this property has to offer. A must see.


40 Photos
LAMACCHIA REALTY, INC
$465,000
5 BD | 3 BA
Residential - Single Family

OPEN HOUSE Sat 11/01/25 11am-12:30pm. This stunning 5-bedroom, 3-bath farmhouse was fully renovated from top to bottom in 2020, offering 2,800 SqFt of stylish, move-in-ready living space in one of Southeast Pittsfield's most desirable neighborhoods. Situated on a generous corner lot, the home makes a striking first impression with its inviting wraparound front porch. A circular driveway provides ample parking and is complimented by a detached one-car garage. Step through the front door into a spacious foyer with sleek hardwood floors throughout the open concept main level. The dining room has enough space for memorable meals and entertaining, while the chef's kitchen is outfitted with stainless steel appliances, a natural gas range, quartz & granite countertops, center island and French


48 Photos
WILLIAM PITT SOTHEBY'S - LENOX
$469,000
4 BD | 4 BA
Residential - Single Family

Step into a world where historic charm meets contemporary living in this unique 4-bedroom, 4-bath Arts & Crafts home located in the heart of Southeast Pittsfield. This one-of-a-kind residence is brimming with character and has been lovingly maintained to showcase its original features while providing all the comforts of Berkshire living. This majestic home has a fascinating origin story. Built in the late 1800s, it was once the east wing of the summer residence of the Pillsbury family. Originally adjoined with the house behind it on Wendell Avenue and situated a half block away, the sprawling grand estate was divided into two separate homes, and carefully moved by horse in the early 1900s, establishing the neighborhood that would grow around them.


56 Photos
GELINAS REAL ESTATE
$469,000
3 BD | 3 BA
Residential - Single Family

Welcome home to this warm and inviting property set in a quiet and desirable Pittsfield neighborhood. With a comfortable flow and plenty of space for gathering, this home is ideal for entertaining and spending time with loved ones, especially as we head into the winter months. Inside, you'll find 3 bedrooms, 2 full baths, and 1,890 sq. ft. of well-designed living space. The cozy downstairs living room features a gas fireplace insert, perfect for chilly evenings, while the open kitchen/dining area, as well as a wet bar make this home an entertainers dream. The heated sun porch off the kitchen offers a bright, relaxing spot to enjoy year-round.


48 Photos
BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
$469,900
3 BD | 2 BA
Residential - Single Family

Welcome to 93 Roselyn Drive, a beautifully maintained, move-in-ready, light-filled mid-century gem with style, function, and effortless upkeep, ideally situated in Pittsfield's desirable west-side neighborhood.This home offers big-sky views and a private 0.75-acre yard - perfect for morning coffee, stargazing, or weekend gatherings on the expansive two-level deck overlooking mature, easy-to-care-for gardens.Inside are sun-filled rooms, a classic stone gas fireplace with remote control, a fabulous bonus room with large windows facing the backyard - ideal for a home office, family room, or yoga studio - plus a newly finished lower level adding more versatility with a full bath, cedar closet, laundry area, and plenty of room for a guest suite, media room, or private gym.


33 Photos
LAMACCHIA REALTY, INC
$469,900
4 BD | 3 BA
Residential - Single Family

Welcome to 59 Joan Drive, a well appointed 4-bedroom, 2.5-bath raised ranch located in one of Pittsfield's premier neighborhoods. The main level boasts a bright living room, a modern kitchen with ample storage, and a dining area that opens to a spacious wrap around deck, ideal for outdoor gatherings. The master suite offers a private full bath, while three additional bedrooms provide plenty of space for family or guests. The finished lower level includes a versatile family room, 1/2 bath, laundry room and access to the 2 car garage. Perfectly set on approx .42 acres of land this property offers mountain views, yet in a neighborhood setting. This home comes with a one year transferable home warranty, whole house water filter and additional insulation was just added to increase efficiency.


38 Photos
LAMACCHIA REALTY, INC
$475,000
3 BD | 3 BA
Residential - Single Family

Step into this beautifully renovated home, where classic charm meets modern convenience. Located in desirable Southeast Pittsfield, this home boasts a brand-new kitchen with sleek countertops, state-of-the-art appliances, and fresh paint throughout. Both bathrooms have been tastefully remodeled with contemporary finishes, elevating the overall style and comfort.Two expansive living rooms offer plenty of space for relaxation and entertainment, including one with a cozy wood-burning fireplace and original built-in cabinetry. Upstairs, the primary bedroom features a spacious walk-in closet and offers versatile space perfect for a sitting area, office, or nursery.


44 Photos
WILLIAM PITT SOTHEBY'S - LENOX

Dottie's Coffee Lounge & Dorothy's Estaminet, a beloved staple in the heart of Berkshire County, is now presenting a rare opportunity for new ownership. Renowned for its commitment to sustainability and locally sourced offerings, this legendary establishment has served as a community hub for food enthusiasts, coffee connoisseurs, and art and music lovers alike. This ethos has cultivated a loyal customer base and contributed to a sustainable community that values the connection between local produce, culinary excellence, and culture. This is more than a business transaction; it's a chance to carry on a legacy that has been an integral part of Berkshire County's fabric. *Sale is for the business & fixtures only-does not include real estate.

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